People often ask me and my wife what gave us the confidence to quit our comfy professional lives in Canada to open a small-group tour company in the Abruzzo region of Italy?
It’s a good question. We knew selling everything we owned and investing in a historic villa, vans, and everything else needed run the business was a risk. But we always thought we had a pretty good chance at success.
Why though?
Neither of us had experience in the tourism business. She was a lawyer and I was a former journalist and municipal bureaucrat. That doesn’t translate into a guaranteed bet – and it was about a $500,000 wager without factoring in the foregone income and pensions.
Sure, we’d done our homework thoroughly. Almost all risk-takers are really risk-minimizers, and we were no exception. We had financial, marketing, operating and start-up plans. We’d consulted dozens of people. We even did a strength, weakness, opportunity and threat analysis.
A guest got married at our place a few years ago. She rode to her wedding ceremony on a donkey as is tradition in Abruzzo. Last year she came back and asked she could have a visit with a donkey. We delivered right in our Villa’s back yard.
That’s all well and good. We thought the business would work. OK. But why did we – Jake Rupert and Lisa Grassi Blais – think WE could do it?
The answer occurred to me recently when we decided it was time to open a second location in the town of Torre de’Passeri, about 150 kilometers east of Rome and 40 kilometers inland west of the Adriatic Sea.
I was having a moment of angst about an aspect of the plan and I told Lisa.
“We’ll deal with that,” she said. “We done things way more difficult than this before. Whatever it is, we’ll figure it out. We always do.”
It’s true. We go into things confident we’ll be up to the tasks, and I think it’s because of our histories.
I spent the first 12 years of my life on a working farm with parents who encouraged me to be and think independently. We had cows, pigs, chickens, tractors, plows, discs, balers, wagons, hay fields, corn fields etc. On farms you need all hands working, even small hands. So, from a young age, I had big responsibilities — like driving tractors at six years old. I’m not kidding. At first my dad would get a tractor going dragging the discs then jump off leaving me to follow him on his tractor pulling the plow.
Lisa and I on one of our walks near our house in Abruzzo. We have confidence in ourselves as indaviduals and in each other. It’s allowed us to live the lives we wanted.
There was no power steering on these tractors. I would have to go to one side of the steering wheel or the other and put all my strength and weight into pulling the wheel down to get the tractor to turn. To stop, I would go to the left side of the wheel, push in the clutch with all my strength and shift the gear to neutral, then go around the other side of the wheel and jump on the brake pedal.
I shudder to think what child protection services would think about that these days.
Before school, I would get up at 6 a.m. and trudge to the barn for chores. Hay and molasses for the cows. Pellets for the pigs. Cracked corn meal for the chickens. Scape down the cow shit, turn on the gutter cleaner system, fresh straw under the cows. There was no time for a shower before the school bus arrived, so I smelt like cow shit, but it didn’t matter every other farm boy on the bus did too.
Much of the farm work, I did alone. If something broke down, I had to figure out how to fix it. On a farm, you don’t call a handyman, you are the handyman. If a cow was in distress, I tried to figure out what was wrong. If the steers wouldn’t come back in the barn, I rounded them up. Tractor wouldn’t start, check the plugs and battery. If it needs a boost or a new plug, do it.
You wouldn’t believe how long it took to have all five of us looking at the camera at the same time.
On a farm, you learn to get things done. More so, you learn that you can do them. From a young age, I’ve had confidence that whatever the task or challenge, I can figure it out or throw my literal or proverbial muscle at it, and things will generally work out. I’ve done it all my life.
Lisa’s confidence comes from a different place: she’s driven to succeed.
I’m a guy whose parents provided a cushy first 20 years with lots of opportunity. I took my privileged position for granted and squandered opportunities in different ways until I finally matured at around 25.
Not Lisa. She has had to work her ass off for everything she’s achieved.
Her mother, a true survivor, and Lisa lived in a cottage without running water one winter. After school, there was no babysitter. Instead, Lisa would head to the courthouse where her mother worked as a court reporter and sit in the pews watching the proceedings or doing her homework.
It was during this period, like when she was nine years old, that Lisa decided she would be a lawyer; not wanted to be a lawyer, would be a lawyer.
Lisa excelled in high school even though she will tell you that she wasn’t a naturally gifted student. Instead, she worked as hard as she could. (Oh ya, I forgot, she did high school in French. Her second language.) She got into university, which she and her mother paid for with meagre savings and student loans.
She plowed through undergrad with decent, but not spectacular grades. When it came time to apply to law school, she applied to a French program as there was less competition for spots. She got in, again plowed through, and became the president of her class. She passed the bar, having to take one test twice. She worked full time in summers and part time during the school year.
After the bar, she got a job in a law firm with dozens of male lawyers and two females. She went into the male dominated field of criminal law. She excelled in court. She left her home city and moved to another with more opportunity. She made that work too.
Lisa is so driven to succeed; she sometimes doesn’t know when she can stop and pushes for perfection.
For example, she once defended a notorious hood who, in front of dozens of people in a nightclub, pulled a knife, chased down another guy and stabbed him. Turns out none of the holes her client poked in the guy were fatal, so he was only charged with attempted murder. The Crown thought it was and open and shut case, but after Lisa got done cross examining the cops, witnesses and alleged victim, the case lay in tatters, and her client was convicted of common assault.
Big success, right? Nope, Lisa was mad that he wasn’t found innocent.
I remember saying to her:
“He stabbed a guy in front of a crowd of witnesses. Did you want the judge to give him a medal?”
She smiled.
“Maybe just a small one.”
Lisa is used to succeeding regularly through sheer will. She is confident she can get things done no matter how difficult the challenges. She knows this because she’s been doing it all her life.
You put us together and you get two capable people who aren’t afraid of a challenge, or failing at a challenge either, because we have confidence in ourselves.
That’s why we thought WE– Lisa Grassi Blais and Jake Rupert – could chuck our comfy lives in North America to live a more relaxing life in pastural foothills of rural Abruzzo, Italy. That’s why last year, we decided to open another location. There might be problems looming, but we’ll solve them.
We might not be the sharpest or most talented people around, but we believe in ourselves enough to think that if we work together, there’s almost no challenge we can’t meet.
